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p-Toluidine → 3-(7-Isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-4-(4-methoxy-phenylsulfanyl)-N-p-tolyl-benzamide

HRID 605170
Notes
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Reaction equation

HRID 605170 reaction equation
[CH:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:12]([NH:13][C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=3[S:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[C:17](Cl)=[O:18])=[N:11][CH:10]=[N:9][C:8]=2[N:32]=1)([CH3:3])[CH3:2].[NH2:33][C:34]1[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=1.C(N(CC)CC)C>ClCCl>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:12]([NH:13][C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=3[S:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[C:17]([NH:33][C:34]3[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=3)=[O:18])=[N:11][CH:10]=[N:9][C:8]=2[N:32]=1)([CH3:3])[CH3:2]
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7813p-ToluidineHCID 8471TriethylamineHCID 866155503-(7-Isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-4-(4-methoxy-phenylsulfanyl)-benzoyl chloride

Product 1

HCID 670405303-(7-Isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-4-(4-methoxy-phenylsulfanyl)-N-p-tolyl-benzamide

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To the product from Example 137B (70 mg, 0.1505 mmol) was treated with p-toluidine (16 mg, 0.1505 mmol), triethylamine (0.025 mL, 0.1806 mmol) and dichloromethane (4 mL) following the procedure from Example 137C to provide the title compound as an off white solid after chromatography (64 mg, 80%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.34 (d, J=6.62 Hz, 6 H) 2.27 (s, 3 H) 3.17-3.30 (m, 1 H) 3.78 (s, 3 H) 7.00 (d, J=8.82 Hz, 2 H) 7.14 (d, J=8.09 Hz, 2 H) 7.40 (d, J=8.82 Hz, 2 H) 7.62 (d, J=8.46 Hz, 1 H) 7.80 (d, J=8.09 Hz, 1 H) 7.99 (s, 1 H) 8.59 (s, 1 H) 8.86 (d, J=8.46 Hz, 1 H) 10.13 (s, 1 H) 10.20 (s, 1 H); MS (APCI) m/z 536 (M+H)+.

Sources & evidence

ORD record
ord-a7765eef478446fdae02b23b5196d533
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07910595B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes